Ornidazole

Not to be confused with ronidazole.

Ornidazole
Clinical data

Trade names	Xynor
AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	G01AF06 (WHO) J01XD03 (WHO) P01AB03 (WHO) QP51AA03 (WHO)
Pharmacokinetic data
Metabolism	Metabolized via the liver, excreted in the Urine and Feces
Excretion	85% of single oral dose is eliminated with 5 days - Urine (63%) and Feces (22%)
Identifiers
IUPAC name 1-Chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol
CAS Number	16773-42-5^Y
PubChem (CID)	28061
ChemSpider	26102^Y
UNII	62XCK0G93T^Y
KEGG	D05274^Y
ChEBI	CHEBI:75176^N
ChEMBL	CHEMBL1449676^N
ECHA InfoCard	100.037.099
Chemical and physical data
Formula	C₇H₁₀ClN₃O₃
Molar mass	219.625 g/mol
3D model (Jmol)	Interactive image
SMILES [O-][N+](=O)c1cnc(n1CC(O)CCl)C
InChI InChI=1S/C7H10ClN3O3/c1-5-9-3-7(11(13)14)10(5)4-6(12)2-8/h3,6,12H,2,4H2,1H3^Y Key:IPWKIXLWTCNBKN-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

Ornidazole is a drug that cures some protozoan infections. It has been investigated for use in Crohn's disease after bowel resection.^[1]

Synthesis is a straightforward reaction between 2-methyl-nitroimidazole and epichlorohydrin under acid catalyst conditions.^[2]

Mechanism Of Action & Susceptible Organisms

After passive absorption into bacterium cell, the nitro group of ornidazole is reduced to amine group by ferrodoxin type redox system. The formation of redox intermediate intracellular metabolites is believed to be the key component of microorganism killing for Ornidazole. The drug is active against anaerobic bacteria viz. Peptostreptococcus, Clostridium, B. fragilis, Prevotella, Porphyronomas, Fusobacterium and protozoa viz. E. histolytica, T. vaginalis, G. intestinalis etc.^[3]

References

↑ Rutgeerts P, Van Assche G, Vermeire S, et al. (April 2005). "Ornidazole for prophylaxis of postoperative Crohn's disease recurrence: a randomized, double-blind, placebo-controlled trial". Gastroenterology. 128 (4): 856–61. doi:10.1053/j.gastro.2005.01.010. PMID 15825069.
↑ Hoffer, Max; Grunberg, Emanuel (1974). "Synthesis and antiprotozoal activity of 1-(3-chloro-2-hydroxypropyl)-substituted nitroimidazoles". Journal of Medicinal Chemistry. 17 (9): 1019–1020. doi:10.1021/jm00255a026. ISSN 0022-2623.
↑ http://webcache.googleusercontent.com/search?q=cache:OFkC_pjHLZ4J:www.panacea-biotec.com/product-pdf/Ocimix_28-11-2010.pdf

Antibacterials: nucleic acid inhibitors (J01E, J01M)

Antifolates
(inhibits
purine metabolism,
thereby inhibiting
DNA and RNA synthesis)

DHFR inhibitor

2,4-Diaminopyrimidine
- Trimethoprim^#
- Brodimoprim
- Tetroxoprim
- Iclaprim^†

Sulfonamides
(DHPS inhibitor)

Short- acting	Sulfaisodimidine Sulfamethizole Sulfadimidine Sulfapyridine Sulfafurazole Sulfanilamide Prontosil Sulfathiazole Sulfathiourea

Intermediate- acting	Sulfamethoxazole Sulfadiazine^# Sulfamoxole

Long- acting	Sulfadimethoxine Sulfadoxine Sulfalene Sulfametomidine Sulfametoxydiazine Sulfamethoxypyridazine Sulfaperin Sulfamerazine Sulfaphenazole Sulfamazone

Other/ungrouped	Sulfacetamide Sulfadicramide Sulfametrole

Combinations

Trimethoprim/sulfamethoxazole^#

Topoisomerase
inhibitors/
quinolones/
(inhibits
DNA replication)

1st g.

Fluoro-
quinolones

2nd g.	Ciprofloxacin^# Ofloxacin Enoxacin^‡ Fleroxacin^‡ Lomefloxacin^‡ Nadifloxacin^‡ Norfloxacin^‡ Pefloxacin^‡ Rufloxacin^‡

3rd g.	Levofloxacin Balofloxacin^‡ Grepafloxacin^‡ Pazufloxacin^‡ Sparfloxacin^‡ Temafloxacin^‡ Tosufloxacin^‡

4th g.	Besifloxacin Gatifloxacin Finafloxacin Gemifloxacin Moxifloxacin Clinafloxacin^† Garenoxacin^‡ Prulifloxacin^‡ Sitafloxacin^‡ Trovafloxacin^‡/Alatrofloxacin^‡

Vet.	Danofloxacin Difloxacin Enrofloxacin Ibafloxacin Marbofloxacin Orbifloxacin Pradofloxacin Sarafloxacin

Newer non-fluorinated

Nemonoxacin

Related (DG)

Aminocoumarins: Novobiocin

Anaerobic DNA
inhibitors

Nitro- imidazole derivatives	Metronidazole^# Tinidazole Ornidazole

Nitrofuran derivatives	Nitrofurantoin^# Furazolidone^‡ Nifurtoinol

RNA synthesis

Rifamycins/ RNA polymerase	Rifampicin^# Rifabutin Rifapentine Rifaximin Rifalazil^§

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Gynecological anti-infectives and antiseptics (G01)

Antibiotics

Arsenic compounds

Acetarsol

Quinoline derivatives

Organic acids

Sulfonamides

Sulfatolamide

Antifungals

Imidazoles	Metronidazole Clotrimazole Miconazole Econazole Ornidazole Isoconazole Tioconazole Ketoconazole Fenticonazole Azanidazole Propenidazole Butoconazole Omoconazole Oxiconazole Flutrimazole

Triazoles	Terconazole

Polyenes	Nystatin Natamycin Amphotericin B

Other	Ciclopirox Methylrosaniline

Other

Antiparasitics – antiprotozoal agents – agents against amoebozoa/amebicide (P01)

Entamoeba

Tissue amebicides

Nitroimidazole derivatives	Metronidazole^# Tinidazole Ornidazole Nimorazole Secnidazole Azanidazole Propenidazole

Other	isoquinoline (Emetine/Dehydroemetine)

Luminal amebicides

Hydroxyquinoline derivatives	Cl (Chlorquinaldol) Br (Tilbroquinol Broxyquinoline) I (Diiodohydroxyquinoline) I, Cl (Clioquinol) related: Chiniofon

Dichloroacetamide derivatives	Diloxanide^# Clefamide Etofamide Teclozan

Aminoglycoside	Paromomycin

Other/ungrouped

Acanthamoeba

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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